Water → N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl ester

HRID 2084931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2084931
Cl.[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:18]#[C:19][CH3:20].O>ClCCl>[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:6][CH:5]([CH2:7][OH:8])[C:4]([O:3][CH3:2])=[O:9])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:18]#[C:19][CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 11446470D-Serine methyl ester hydrochloride

Produkt 1

HCID 12016494N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl esterAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a 0° solution of D-serine methyl ester hydrochloride (0.62 g, 4 mmol) in 5 mL of dichloromethane was added triethylamine (1.67 mL, 12 mmol) followed by a dichloromethane (6 mL) solution of 4-(2-butynyloxy)-benzenesufonyl chloride (0.98 g, 4 mmol). The reaction was stirred at room temperature overnight and then the mixture was poured into water. The organic layer was washed with 2N citric acid, water and brine, dried over sodium sulfate, filtered and concentrated to give 1.16 g of methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-hydroxypropanoate. Yield˜89.2%. mp 72-74° C. Electrospray Mass Spec 328.2 (M+H)+.

Aufarbeitung

  1. washThe organic layer was washed with 2N citric acid, water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9c02a0962fe743a98129bc2f631f95c2
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716833B2

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